Chloroform → 6-(5-Cholesten-3beta-yloxy)hexyl 6-amino-6-deoxy-1-thio-beta-D-galactopyranoside

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Reaction Steps

A suspension of 6-(5-cholesten-3β-yloxy)hexyl 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-β-D-galactopyranoside (710 mg.) in methanol (10 ml.) and n-butylamine (10 ml.) is heated under reflux for 16 hours. The solution is evaporated to a crystalline mass. Chloroform is added and the solid is filtered and washed with chloroform. The combined filtrates are evaporated to a syrup which is put on a column of silica gel and eluted with chloroform-methanol-ammonium hydroxide (80:20:2). The desired fractions are combined and evaporated to a syrup which is triturated with ethyl ether to give crystals (390 mg. 76%); Rf 0.28 (CHCl3 --MeOH--NH4OH, 80:20:2), [α]D27 -29.5° C. (C 1.05, chloroform), m.s.: m/e 665 (M+ +1).

Provenance & Evidence